ContaminantDB: Chromium(III) acetylacetonate

Identification Taxonomy Biological Properties Physical Properties Toxicity Profile Spectra Concentrations Links References Targets (5)XML

Record Information

Version

1.0

Creation Date

2009-06-19 21:58:47 UTC

Update Date

2026-04-05 20:08:17 UTC

Accession Number

CHEM001229

Identification

Common Name

Chromium(III) acetylacetonate

Class

Small Molecule

Description

Chromium(III) acetylacetonate is a coordination complex of chromium. It is used in NMR spectroscopy as a relaxation agent. Chromium is a chemical element which has the symbol Cr and atomic number 24. It is found naturally occuring in rocks, animals, plants, and soil, and is usually mined as chromite ore. Chromium is most toxic in its +6 oxidation state (chromium(VI)) due to its greater ability to enter cells and higher redox potential. Trivalent chromium (chromium(III)) however, is biologically necessary for sugar and lipid metabolism in humans. (6, 8)

Contaminant Sources

IARC Carcinogens Group 3
T3DB toxins
ToxCast & Tox21 Chemicals

Contaminant Type

Chromium Compound
Ester
Industrial/Workplace Toxin
Organic Compound
Organometallic
Pollutant
Synthetic Compound

Chemical Structure

MOL SDF PDB SMILES InChI

Synonyms

Value	Source
Chromium(III) acetylacetonic acid	Generator

Chemical Formula

C₁₅H₂₁CrO₆

Average Molecular Mass

349.320 g/mol

Monoisotopic Mass

349.074 g/mol

CAS Registry Number

21679-31-2

IUPAC Name

(3Z)-4-{[bis({[(2Z)-4-oxopent-2-en-2-yl]oxy})chromio]oxy}pent-3-en-2-one

Traditional Name

(3Z)-4-{[bis({[(2Z)-4-oxopent-2-en-2-yl]oxy})chromio]oxy}pent-3-en-2-one

SMILES

CC(=O)\C=C(\C)O[Cr](O\C(C)=C/C(C)=O)O\C(C)=C/C(C)=O

InChI Identifier

InChI=1S/3C5H8O2.Cr/c3*1-4(6)3-5(2)7;/h3*3,6H,1-2H3;/q;;;+3/p-3/b3*4-3-;

InChI Key

JWORPXLMBPOPPU-LNTINUHCSA-K

Chemical Taxonomy

Description

belongs to the class of organic compounds known as enones. Enones are compounds containing the enone functional group, with the structure RC(=O)CR'.

Kingdom

Organic compounds

Super Class

Organic oxygen compounds

Class

Organooxygen compounds

Sub Class

Carbonyl compounds

Direct Parent

Enones

Alternative Parents

Substituents

Vinylogous acid
Enone
Acryloyl-group
Ketone
Organic transition metal salt
Enolate
Organic chromium salt
Organic oxide
Hydrocarbon derivative
Organic salt
Aliphatic acyclic compound

Molecular Framework

Not Available

External Descriptors

Not Available

Biological Properties

Status

Detected and Not Quantified

Origin

Exogenous

Cellular Locations

Cytoplasm
Extracellular

Biofluid Locations

Not Available

Tissue Locations

Not Available

Pathways

Not Available

Applications

Not Available

Biological Roles

Not Available

Chemical Roles

Not Available

Physical Properties

State

Solid

Appearance

White powder.

Experimental Properties

Property	Value
Melting Point	Not Available
Boiling Point	Not Available
Solubility	Not Available

Predicted Properties

Property	Value	Source
Water Solubility	0.016 g/L	ALOGPS
logP	2.61	ALOGPS
logP	0.31	ChemAxon
logS	-4.4	ALOGPS
pKa (Strongest Acidic)	18.94	ChemAxon
pKa (Strongest Basic)	-4.7	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	6	ChemAxon
Hydrogen Donor Count	0	ChemAxon
Polar Surface Area	78.9 Å²	ChemAxon
Rotatable Bond Count	9	ChemAxon
Refractivity	82.27 m³·mol⁻¹	ChemAxon
Polarizability	31.69 Å³	ChemAxon
Number of Rings	0	ChemAxon
Bioavailability	1	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	Yes	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

Spectra

Spectrum Type	Description	Splash Key	View
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Positive	splash10-0f89-9007000000-a3e4c0c51a92f2caa67f	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Positive	splash10-001i-9001000000-d83bc2e58dbdf32d4d3a	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Positive	splash10-00lr-9000000000-3445887c19483d799951	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 10V, Negative	splash10-0002-1009000000-7905c97ef104d36b30cc	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 20V, Negative	splash10-052b-9016000000-51d540f014c357163711	Spectrum
Predicted LC-MS/MS	Predicted LC-MS/MS Spectrum - 40V, Negative	splash10-0a4i-9020000000-04d532a6c5aafb9672aa	Spectrum

Toxicity Profile

Route of Exposure

Oral (5) ; inhalation (5) ; dermal (5)

Mechanism of Toxicity

Trivalent chromium may also form complexes with peptides, proteins, and DNA, resulting in DNA-protein crosslinks, DNA strand breaks, DNA-DNA interstrand crosslinks, chromium-DNA adducts, chromosomal aberrations and alterations in cellular signaling pathways. It has been shown to induce carcinogenesis by overstimulating cellular regulatory pathways and increasing peroxide levels by activating certain mitogen-activated protein kinases. It can also cause transcriptional repression by cross-linking histone deacetylase 1-DNA methyltransferase 1 complexes to CYP1A1 promoter chromatin, inhibiting histone modification. Chromium may increase its own toxicity by modifying metal regulatory transcription factor 1, causing the inhibition of zinc-induced metallothionein transcription. (1, 5, 2, 3, 4)

Metabolism

Chromium is absorbed from oral, inhalation, or dermal exposure and distributes to nearly all tissues, with the highest concentrations found in kidney and liver. Bone is also a major storage site and may contribute to long-term retention. Hexavalent chromium's similarity to sulfate and chromate allow it to be transported into cells via sulfate transport mechanisms. Inside the cell, hexavalent chromium is reduced first to pentavalent chromium, then to trivalent chromium by many substances including ascorbate, glutathione, and nicotinamide adenine dinucleotide. Chromium is almost entirely excreted with the urine. (1, 5)

Toxicity Values

Not Available

Lethal Dose

Not Available

Carcinogenicity (IARC Classification)

3, not classifiable as to its carcinogenicity to humans. (7)

Uses/Sources

Chromium(III) acetylacetonate is used in NMR spectroscopy as a relaxation agent. (8)

Minimum Risk Level

Not Available

Health Effects

Chromium in its trivalent state is not very toxic. It may be oxidized to hexavalent chromium, a known carcinogen. Hexavalent chromium has also been shown to affect reproduction and development. (1)

Symptoms

Chromium in its trivalent state is not very toxic, but it may be oxidized to hexavalent chromium. Breathing hexavalent chromium can cause irritation to the lining of the nose, nose ulcers, runny nose, and breathing problems, such as asthma, cough, shortness of breath, or wheezing. Ingestion of hexavalent chromium causes irritation and ulcers in the stomach and small intestine, as well as anemia. Skin contact can cause skin ulcers. (5)

Treatment

There is no know antidote for chromium poisoning. Exposure is usually handled with symptomatic treatment. (5)

Concentrations

Not Available

External Links

DrugBank ID

Not Available

HMDB ID

Not Available

FooDB ID

Not Available

Phenol Explorer ID

Not Available

KNApSAcK ID

Not Available

BiGG ID

Not Available

BioCyc ID

Not Available

METLIN ID

Not Available

PDB ID

Not Available

Wikipedia Link

Chromium(III) acetylacetonate

Chemspider ID

Not Available

ChEBI ID

Not Available

PubChem Compound ID

5484009

Kegg Compound ID

Not Available

YMDB ID

Not Available

ECMDB ID

Not Available

References

Synthesis Reference

Not Available

MSDS

Not Available

General References

Not Available

Chromium(III) acetylacetonate (CHEM001229)

Structure for CHEM001229: Chromium(III) acetylacetonate